Low viscosity, low volatility lubricating oil basestocks

ABSTRACT

This disclosure provides low viscosity, low volatility alkylated siloxane compounds and alkylated alkoxy silane compounds. This disclosure also provides processes for producing the alkylated siloxane compounds and alkylated alkoxy silane compounds, and lubricating oil basestocks and lubricating oils containing one or more of the alkylated siloxane compounds or one or more of the alkylated alkoxy silane compounds. This disclosure further provides a method for improving one or more of solubility and dispersancy of polar additives and/or sludge in a lubricating oil by using as the lubricating oil a formulated oil containing one or more of the alkylated siloxane compounds or one or more of the alkylated alkoxy silane compounds.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to U.S. Provisional Application Ser.No. 61/972,463 filed Mar. 31, 2014, which is herein incorporated byreference in its entirety.

FIELD

This disclosure relates to low viscosity, low volatility alkylatedsiloxane compounds or alkylated alkoxy silane compounds, processes forproducing the alkylated siloxane compounds or alkylated alkoxy silanecompounds, lubricating oil basestocks and lubricating oils containingone or more of the alkylated siloxane compounds or one or more of thealkylated alkoxy silane compounds, and a method for improving one ormore of solubility and dispersancy of polar additives and/or sludge in alubricating oil by using as the lubricating oil a formulated oilcontaining one or more of the alkylated siloxane compounds or one ormore of the alkylated alkoxy silane compounds.

BACKGROUND

Lubricants in commercial use today are prepared from a variety ofnatural and synthetic basestocks admixed with various additive packagesand solvents depending upon their intended application. The basestockstypically include mineral oils, polyalphaolefins (PAO), gas-to-liquidbase oils (GTL), silicone oils, phosphate esters, diesters, polyolesters, and the like.

A major trend for passenger car engine oils (PCEOs) is an overallimprovement in quality as higher quality basestocks become more readilyavailable. Typically the highest quality PCEO products are formulatedwith basestocks such as PAOs or GTL stocks.

PAOs and GTL stocks are an important class of lube basestocks with manyexcellent lubricating properties, including high viscosity index (VI)but have low polarity. This low polarity leads to low solubility anddispersancy for polar additives and/or sludge generated during service.These basestocks require the use of cobasestocks to improve additive anddeposit solubility.

Therefore, there is a need for polar cobase fluids that provideappropriate solubility and dispersibility for polar additives and/orsludge generated during service of lubricating oils.

The present disclosure also provides many additional advantages, whichshall become apparent as described below.

SUMMARY

This disclosure provides polar Group V basestocks containing one or morealkylated siloxane compounds or one or more alkylated alkoxy silanecompounds. The alkylated siloxane-containing fluids and alkylated alkoxysilane-containing fluids of this disclosure have surprisingly goodlubricant properties. Moreover, the alkylated siloxane-containing fluidsand alkylated alkoxy silane-containing fluids of this disclosure havesurprisingly lower friction coefficient than PAOs of similar viscosity,thus providing fuel economy advantages. The alkylatedsiloxane-containing fluids and alkylated alkoxy silane-containing fluidsof this disclosure are organic molecules containing hydrocarbon andsiloxy or silane segments with precise structure (i.e., not polymers).

This disclosure relates in part to compositions comprising one or morecompounds represented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; and wherein the composition has aviscosity (Kv₁₀₀) from about 2 to about 300 cst at 100° C., and aviscosity index (VI) from about −100 to about 300; or to compositionscomprising one or more compounds represented by the formula:R₅—Si(OR₆)₃  (2)wherein R₅ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₆ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the olefin is selectedfrom the group consisting of an aliphatic olefin, an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin; and wherein thecomposition has a viscosity (Kv₁₀₀) from about 2 to about 300 cst at100° C., and a viscosity index (VI) from about −100 to about 300.

This disclosure also relates in part to compositions comprising one ormore compounds represented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the composition comprising one or morecompounds represented by formula (1) is produced by a process whichcomprises reacting an alkyl siloxane with an olefin, in the presence ofa catalyst, under reaction conditions sufficient to produce thecomposition; wherein the alkyl siloxane has from about 4 to about 20carbon atoms; and the olefin is selected from the group consisting of analiphatic olefin, an aromatic olefin, a cycloaliphatic olefin, a vinylether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; and wherein the composition has aviscosity (Kv₁₀₀) from about 2 to about 300 cst at 100° C., and aviscosity index (VI) from about −100 to about 300; or to compositionscomprising one or more compounds represented by the formula:R₅—Si(OR₆)₃  (2)wherein R₅ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₆ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the compositioncomprising one or more compounds represented by formula (2) is producedby a process which comprises reacting an alkoxy silane with an olefin,in the presence of a catalyst, under reaction conditions sufficient toproduce the composition; wherein the alkoxy silane has from about 3 toabout 20 carbon atoms; and the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; and wherein the composition has aviscosity (Kv₁₀₀) from about 2 to about 300 cst at 100° C., and aviscosity index (VI) from about −100 to about 300.

This disclosure further relates in part to a process for preparing acomposition comprising one or more compounds represented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the process comprises reacting an alkylsiloxane with an olefin, in the presence of a catalyst, under reactionconditions sufficient to produce the composition; wherein the alkylsiloxane has from about 4 to about 20 carbon atoms; and the olefin isselected from the group consisting of an aliphatic olefin, an aromaticolefin, a cycloaliphatic olefin, a vinyl ether, an acrylate, amethacrylate, a vinyl ester, and a heteroatom-containing olefin; andwherein the composition has a viscosity (Kv₁₀₀) from about 2 to about300 cst at 100° C., and a viscosity index (VI) from about −100 to about300; or to a process for preparing a composition comprising one or morecompounds represented by the formula:R₅—Si(OR₆)₃  (2)wherein R₅ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₆ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the process comprisesreacting an alkoxy silane with an olefin, in the presence of a catalyst,under reaction conditions sufficient to produce the composition; whereinthe alkoxy silane has from about 3 to about 20 carbon atoms; and theolefin is selected from the group consisting of an aliphatic olefin, anaromatic olefin, a cycloaliphatic olefin, a vinyl ether, an acrylate, amethacrylate, a vinyl ester, and a heteroatom-containing olefin; andwherein the composition has a viscosity (Kv₁₀₀) from about 2 to about300 cst at 100° C., and a viscosity index (VI) from about −100 to about300.

This disclosure also relates in part to a lubricating oil basestockcomprising one or more compounds represented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; and wherein the lubricating oil basestockhas a viscosity (Kv₁₀₀) from about 2 to about 300 cst at 100° C., and aviscosity index (VI) from about −100 to about 300; or a lubricating oilbasestock comprising one or more compounds represented by the formula:R₅—Si(OR₆)₃  (2)wherein R₅ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₆ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the olefin is selectedfrom the group consisting of an aliphatic olefin, an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin; and wherein thelubricating oil basestock has a viscosity (Kv₁₀₀) from about 2 to about300 cst at 100° C., and a viscosity index (VI) from about −100 to about300.

This disclosure further relates in part to a lubricating oil comprisinga lubricating oil basestock as a major component, and a lubricating oilcobasestock as a minor component; wherein the lubricating oilcobasestock comprises one or more compounds represented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; and wherein the lubricating oilcobasestock has a viscosity (Kv₁₀₀) from about 2 to about 300 cst at100° C., and a viscosity index (VI) from about −100 to about 300; or alubricating oil comprising a lubricating oil basestock as a majorcomponent, and a lubricating oil cobasestock as a minor component;wherein the lubricating oil cobasestock comprises one or more compoundsrepresented by the formula:R₅—Si(OR₆)₃  (2)wherein R₅ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₆ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the olefin is selectedfrom the group consisting of an aliphatic olefin, an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin; and wherein thelubricating oil cobasestock has a viscosity (Kv₁₀₀) from about 2 toabout 300 cst at 100° C., and a viscosity index (VI) from about −100 toabout 300.

This disclosure yet further relates in part to a method for improvingone or more of solubility and dispersancy of polar additives or sludgein a lubricating oil by using as the lubricating oil a formulated oilcomprising a lubricating oil basestock as a major component, and alubricating oil cobasestock as a minor component; wherein thelubricating oil cobasestock comprises one or more compounds representedby the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; and wherein the lubricating oilcobasestock has a viscosity (Kv₁₀₀) from about 2 to about 300 cst at100° C., and a viscosity index (VI) from about −100 to about 300; or thelubricating oil cobasestock comprises one or more compounds representedby the formula:R₅—Si(OR₆)₃  (2)wherein R₁ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₂ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the olefin is selectedfrom the group consisting of an aliphatic olefin, an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin; and wherein thelubricating oil cobasestock has a viscosity (Kv₁₀₀) from about 2 toabout 300 cst at 100° C., and a viscosity index (VI) from about −100 toabout 300.

In addition to improved solubility and dispersibility for polaradditives and/or sludge generated during service of lubricating oils,improved fuel efficiency can also be attained in an engine lubricatedwith a lubricating oil by using as the lubricating oil a formulated oilin accordance with this disclosure. The formulated oil comprises alubricating oil basestock as a major component, and an alkylatedsiloxane-containing or an alkylated alkoxy silane-containing lubricatingoil cobasestock as a minor component. The lubricating oils of thisdisclosure are particularly advantageous as passenger vehicle engine oil(PVEO) products. Optionally, the formulated oil comprises a lubricatingoil basestock as a minor component, and an alkylated siloxane-containingor an alkylated alkoxy silane-containing, lubricating oil cobasestock asa major component.

Further objects, features and advantages of the present disclosure willbe understood by reference to the following drawings and detaileddescription.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows ¹H NMR spectra for 1-decene starting olefin (top spectrum)and 1,3-didecyl-1,1,3,3-tetramethyl disiloxane (bottom spectrum) forExample 1.

FIG. 2 shows ¹H NMR spectra for 1-dodecene starting olefin (topspectrum) and 1,3-didodecyl-1,1,3,3-tetramethyl disiloxane (bottomspectrum) for Example 2.

FIG. 3 shows ¹H NMR spectra for C₁₆-dimer starting olefin (top spectrum)and 1,3-di(2-hexyldecyl)-1,1,3,3-tetramethyl disiloxane (bottomspectrum) for Example 3.

FIG. 4 graphically shows kinematic viscosity (Kv₁₀₀) cst at 100° C. (xaxis) and TGA (Noack) (y axis) of PAO2, PAO4 and the synthetic fluids ofExamples 1-4.

DETAILED DESCRIPTION OF THE EMBODIMENTS

All numerical values within the detailed description and the claimsherein are modified by “about” or “approximately” the indicated value,and take into account experimental error and variations that would beexpected by a person having ordinary skill in the art.

In an embodiment, this disclosure relates to alkylatedsiloxane-containing or alkylated alkoxy silane-containing Low ViscosityLow Volatility (LVLV) synthetic basestocks. The products exhibit goodlubricant properties.

The compositions of this disclosure possess low viscosity, low Noackvolatility and superior low temperature properties. The compositions ofthis disclosure exhibit excellent bulk flow properties with built-inpolarity. The alkylated siloxane-containing fluids and alkylated alkoxysilane-containing fluids of this disclosure are organic moleculescontaining hydrocarbon and siloxy or silane segments with precisestructure (i.e., not polymers).

As indicated above, the fluids of this disclosure comprise one or morecompounds represented by formula (1):R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; or one or more compounds represented byformula (2):R₅—Si(OR₆)₃  (2)wherein R₁ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₂ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the olefin is selectedfrom the group consisting of an aliphatic olefin, an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin.

The fluids of this disclosure include mixtures. Illustrative mixturesinclude, for example, two or more compounds represented by formula (1);two or more compounds represented by formula (2); and two or morecompounds represented by formula (1) and formula (2).

The fluids of this disclosure have a viscosity (Kv₁₀₀) from about 2 toabout 300 cst at 100° C., and a viscosity index (VI) from about −100 toabout 300. Preferably, the fluids have a viscosity (Kv₁₀₀) from about2.1 to about 250 cst at 100° C., more preferably from 2.2 to 200 cst at100° C., and even more preferably from 2.3 to about 150 cst at 100° C.Preferably, the fluids have a viscosity index (VI) from about −100 toabout 300, more preferably from about 0 to 280, and even more preferablyfrom about 50 to 250. As used herein, viscosity (Kv₁₀₀) is determined byASTM D 445-01, and viscosity index (VI) is determined by ASTM D 2270-93(1998).

The fluids of this disclosure have a Noack volatility of no greater than90 percent, preferably no greater than 80 percent, and more preferablyno greater than about 50 percent. As used herein, Noack volatility isdetermined by ASTM D-5800. In particular, the fluids of this disclosurecan function in engines without volatilization at specific temperatures(e.g., 247-249° C., Noack conditions).

Illustrative R₁, R₂ and R₅ substituents include, for example, theresidue of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, aheteroatom-containing olefin, and the like.

Illustrative aliphatic olefins include, for example, alkyl olefins(C₆-C₄₀) and polyalphaolefin oligomers (C₆-C₄₀). Illustrative alkylolefins include, for example, 1-hexene, 1-octene, 1-decene, 1-dodecene,1-tetradecene, 1-hexadecene, 1-octadecene, and the like. Illustrativepolyalphaolefin oligomers include, for example, mPAO dimer (C₆-C₄₀),trimer (C₆-C₄₀), tetramer (C₆-C₄₀), pentamer (C₆-C₄₀), hexamer (C₆-C₄₀),and the like.

Illustrative aromatic olefins include, for example, 2,4-dimethylstyrene,2,5-dimethylstyrene, 4-tert-butylstyrene, 4-tert-butoxystyrene,3,4-dimethoxystyrene, 4-acetoxystyrene, 1,3-diisopropenylbenzene,4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene, 4-fluorostyrene,1-(trifluoromethyl)-4-vinylbenzene,4-[N-(methylaminoethyl)aminomethyl]styrene,4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol,((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene,2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methylstyrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene,2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene,1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene,1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole,N-vinylphthalimide, 4-(trifluoromethyl)styrene, and the like.

Illustrative cycloaliphatic olefins include, for example,vinylcyclopentane, vinylcylcohexane, cyclopentene, cyclohexene,cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclododecene,cyclotetradecene, cyclohexadecene, cyclooctadecene, allylcyclohexane,1,2,4-trivinylcyclohexane, 5-vinyl-2-norbornene, and the like.

Illustrative vinyl ethers include, for example, ethyl vinyl ether,propyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether,2-ethylhexyl vinyl ether, dodecyl vinyl ether, tetraethylene glycolmethyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether,isooctyl vinyl ether, t-butyl vinyl ether, phenyl vinyl ether,cyclohexyl vinyl ether, 2,2,2-trifluoroethyl vinyl ether, 1,4-butanedioldivinyl ether, di(ethylene glycol) divinyl ether, tri(ethylene glycol)divinyl ether, 1,4-cyclohexanedimethanol divinyl ether,bis[4-(vinyloxy)butyl]isophthalate, bis[4-(vinyloxy)butyl] succinate,diethyl vinyl orthoformate, di(ethylene glycol) vinyl ether, ethyleneglycol vinyl ether, 1,4-butanediol vinyl ether, and the like.

Illustrative acrylates include, for example, methyl acrylate, ethylacrylate, hexyl acrylate, isooctyl acrylate, isodecyl acrylate, laurylacrylate, octadecyl acrylate, di(ethylene glycol) 2-ethylhexyl etheracrylate, di(ethylene glycol) ethyl ether acrylate, ethylene glycolphenyl ether acrylate, 2-ethylhexyl acrylate, butyl acrylate, isobornylacrylate, ethylene glycol methyl ether acrylate, 2-(dimethylamino)ethylacrylate, 2-(diethylamino)ethyl acrylate, 3-(dimethylamino)propylacrylate, pentafluorophenyl acrylate, 1,6-hexanediol diacrylate,trimethylolpropane triacrylate, 4-acetoxyphenethyl acrylate,4-allyloxy-2-hydroxybenzophenone, 2-(4-benzoyl-3-hydroxyphenoxy)ethylacrylate, 4-acryloylmorpholine, 4-tert-butylcyclohexyl acrylate,tetrahydrofurfutyl acrylate, 3,5,5-trimethylhexyl acrylate,di(trimethylolpropane) tetraacrylate,tris[2-(acryloyloxy)ethyl]isocyanurate, pentaerythritol tetraacrylate,1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione,1,3,5-triacryloylhexahydro-1,3,5-triazine,1,1,1,3,3,3-hexafluoroisopropyl acrylate, 9H-carbazole-9-ethyl acrylate,2-hydroxypropyl 2-(methacryloyloxy)ethyl phthalate, and the like.

Illustrative methacrylates include, for example, methyl methacrylate,butyl methacrylate, tert-butyl methacrylate, hexyl methacrylate,2-ethylhexyl methacrylate, 2-(dimethylamino)ethyl methacrylate,2-(diethylamino)ethyl methacrylate, di(ethylene glycol) methyl ethermethacrylate, lauryl methacrylate, stearyl methacrylate, isobornylmethacrylate, ethylene glycol phenyl ether methacrylate, phenylmethacrylate, cyclohexyl methacrylate, allyl methacrylate, vinylmethacrylate, benzyl methacrylate, 1,6-hexanediol dimethacrylate,bisphenol A dimethacrylate, bisphenol A glycerolate dimethacrylate,2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate,cyclohexyl methacrylate, tetrahydrofurfutyl methacrylate,2-(tert-butylamino)ethyl methacrylate, 2-(diisopropylamino)ethylmethacrylate, 2-N-morpholinoethyl methacrylate, 9H-carbazole-9-ethylmethacrylate, 1-naphthyl methacrylate, pentafluorophenyl methacrylate,1-pyrenemethayl methacrylate, TEMPO methacrylate,N-(triphenylmethyl)methacrylamide, and the like.

Illustrative vinyl esters include, for example, vinyl acetate, vinylpropionate, vinyl valerate, vinyl butyrate, vinyl decanoate, vinylstearate, vinyl cinnamate, allyl butyrate, vinyl pivalate, vinylbenzoate, vinyl 4-t-butylbenzoate, allyl cinnamate, and the like.

Illustrative heteroatom-containing olefins include, for example,N-methyl-N-vinylacetamide, N,N-dimethylacrylamide, 4-vinylpyridine,2-vinylpyridine, 1-vinyl-2-pyrrolidinone, 1-vinyl-1,2,4-triazole,1-vinylimidazole, N-vinylcaprolactone, 4-acryloylmorpholine,5-vinyluracil, 4-acryloylmorpholine, N,N-dimethylacrylamide,2-vinyl-1,3-dioxolane, acrolein diethyl acetal, acrolein dimethylacetal, 4-vinyl-1,3-dioxolane-2-one, vinylbenzoic acid, 1-vinylbenzylalcohol, vinyl trifluoroacetate, 1-vinyl cyclohexanole, vinyloxytrimethylsilane, vinyltrimethylsilane, allyl trimethylsilane,triphenyl(vinyl)silane, 2-isopropenyl-2-oxazoline, and the like.

Illustrative R₃, R₄ and R₆ substituents include, for example, linear orbranched alkyl groups having from 1 to about 20 carbon atoms, preferablylinear or branched alkyl groups having from 1 to 10 carbon atoms, andmore preferably linear or branched alkyl groups having from 1 to about 8carbon atoms. Illustrative R₃, R₄ and R₆ substituents include, forexample, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, andthe like.

Illustrative compounds of formula (1) include, for example thoserepresented by the formula:

Illustrative compounds of formula (2) include, for example thoserepresented by the formula:

The compositions comprising one or more compounds represented by formula(1) of this disclosure can be prepared by a process that involvesreacting an alkyl siloxane with an olefin. The reaction is carried outin the presence of a catalyst. The reaction is also carried out underreaction conditions sufficient to produce a composition comprising oneor more compounds represented by formula (1).

Illustrative alkyl siloxanes useful in the process of this disclosureinclude, for example, 1,1,3,3-tetramethyldisiloxane,1,1,3,3-tetramethyldisilazane, 1,3-didecyl-1,1,3,3-tetramethyldisiloxane, 1,3-didodecyl-1,1,3,3-tetramethyl disiloxane,3-di(2-hexyldecyl)-1,1,3,3-tetramethyl disiloxane,1,3-bis(3-(2-hydroxyethyoxy)propyl)tetramethyldisiloxane,1,3-bis(hydroxypropyl)tetramethyldisiloxane,bis(methoxytriethyleneoxypropyl)tetramethyldisiloxane,1,3-bis(trimethylsiloxy)1,3-dimethyldisiloxane,1,3-bis(heptadecafluoro-1,1,2,2-tetrahydrodecyl)tetramethyldiloxane,1,3-bis(3-hydroxyisobutyl)tetramethyldisiloxane,1,3-di-n-butyltetramethyldiloxane, 1,3-diallyltetramethyldisiloxane, andthe like.

Illustrative olefins useful in the process of this disclosure include,for example, aliphatic olefins, aromatic olefins, cycloaliphaticolefins, vinyl ethers, acrylates, methacrylates, vinyl esters,heteroatom-containing olefins, and the like. Illustrative of sucholefins are described herein.

Preferred olefins include aliphatic olefins, for example, alkyl olefins(C₆-C₄₀) and polyalphaolefin oligomers (C₆-C₄₀). Illustrative alkylolefins include, for example, 1-hexene, 1-octene, 1-decene, 1-dodecene,1-tetradecene, 1-hexadecene, 1-octadecene, and the like. Illustrativepolyalphaolefin oligomers include, for example, mPAO dimer (C₆-C₄₀),trimer (C₆-C₄₀), tetramer (C₆-C₄₀), pentamer (C₆-C₄₀), hexamer (C₆-C₄₀),and the like.

Illustrative catalysts that can be used in the process of thisdisclosure include, for example, metal oxide catalysts such as platinumoxide, and the like. The catalyst can be used in conventional amountsneeded to catalyze the reaction of the alkyl siloxane and the olefin.

Other illustrative reaction ingredients include, for example, solventssuch as toluene, xylene, decane, hexane, heptanes, and the like.

Reaction conditions for the reaction of the alkyl siloxane and theolefin, such as temperature, pressure and contact time, may also varygreatly and any suitable combination of such conditions may be employedherein. The reaction temperature may range between about 25° C. to about250° C., and preferably between about 30° C. to about 200° C., and morepreferably between about 60° C. to 150° C. Normally the reaction iscarried out under ambient pressure and the contact time may vary from amatter of seconds or minutes to a few hours or greater. The reactantscan be added to the reaction mixture or combined in any order. The stirtime employed can range from about 0.5 to about 48 hours, preferablyfrom 1 to 36 hours, and more preferably from about 2 to 24 hours.

The compositions comprising one or more compounds represented by formula(2) of this disclosure can be prepared by a process that involvesreacting an alkoxy silane with an olefin. The reaction is carried out inthe presence of a catalyst. The reaction is also carried out underreaction conditions sufficient to produce a composition comprising oneor more compounds represented by formula (2).

Illustrative alkoxy silanes include, for example, trimethoxysilane,triethoxysilane, tetraphenoxysilane, triethoxy(octyl)silane,dodecyltriethoxysilane, hexadecyltrimethoxysilane,1H,1H,2H,2H-perfluorooctyltriethoxysilane,1H,1H,2H,2H-perfluorodecyltriethoxysilane, tetradecamethylhexasiloxane,11-acetoxyundecyltriethoxysilane, 11-allyloxyundecyltrimethoxysilane,isooctyl trimethoxysilane, triethoxy phenylsilane, (trimethyoxysily)cyclohexane, and the like.

Illustrative olefins useful in the process of this disclosure include,for example, aliphatic olefins, aromatic olefins, cycloaliphaticolefins, vinyl ethers, acrylates, methacrylates, vinyl esters,heteroatom-containing olefins, and the like. Illustrative of sucholefins are described herein.

Preferred olefins include aliphatic olefins, for example, alkyl olefins(C₆-C₄₀) and polyalphaolefin oligomers (C₆-C₄₀). Illustrative alkylolefins include, for example, 1-hexene, 1-octene, 1-decene, 1-dodecene,1-tetradecene, 1-hexadecene, 1-octadecene, and the like. Illustrativepolyalphaolefin oligomers include, for example, mPAO dimer (C₆-C₄₀),trimer (C₆-C₄₀), tetramer (C₆-C₄₀), pentamer (C₆-C₄₀), hexamer (C₆-C₄₀),and the like.

Illustrative catalysts that can be used in the process of thisdisclosure include, for example, metal oxide catalysts such as platinumoxide, chloroplatinic acid hydrate H₂[PtCl₆].6H₂O, and the like. Thecatalyst can be used in conventional amounts needed to catalyze thereaction of the alkoxy silane and the olefin.

Other illustrative reaction ingredients include, for example, solventssuch as toluene, xylene, decane, hexane, heptanes, 2-propanol, and thelike.

Reaction conditions for the reaction of the alkoxy silane and theolefin, such as temperature, pressure and contact time, may also varygreatly and any suitable combination of such conditions may be employedherein. The reaction temperature may range between about 25° C. to about250° C., and preferably between about 30° C. to about 200° C., and morepreferably between about 60° C. to 150° C. Normally the reaction iscarried out under ambient pressure and the contact time may vary from amatter of seconds or minutes to a few hours or greater. The reactantscan be added to the reaction mixture or combined in any order. The stirtime employed can range from about 0.5 to about 48 hours, preferablyfrom 1 to 36 hours, and more preferably from about 2 to 24 hours.

Examples of techniques that can be employed to characterize thecompositions formed by the process described above include, but are notlimited to, analytical gas chromatography, nuclear magnetic resonance,thermogravimetric analysis (TGA), inductively coupled plasma massspectrometry, differential scanning calorimetry (DSC), volatility andviscosity measurements.

This disclosure provides lubricating oils useful as engine oils and inother applications characterized by excellent solvency and dispersancycharacteristics. The lubricating oils are based on high qualitybasestocks including a major portion of a hydrocarbon base fluid such asa PAO or GTL with a secondary cobasestock component which is analkylated siloxane-containing fluids or an alkylated alkoxysilane-containing fluid as described herein. The lubricating oilbasestock can be any oil boiling in the lube oil boiling range,typically between 100 to 450° C. In the present specification andclaims, the terms base oil(s) and basestock(s) are used interchangeably.

The viscosity-temperature relationship of a lubricating oil is one ofthe critical criteria which must be considered when selecting alubricant for a particular application. Viscosity Index (VI) is anempirical, unitless number which indicates the rate of change in theviscosity of an oil within a given temperature range. Fluids exhibitinga relatively large change in viscosity with temperature are said to havea low viscosity index. A low VI oil, for example, will thin out atelevated temperatures faster than a high VI oil. Usually, the high VIoil is more desirable because it has higher viscosity at highertemperature, which translates into better or thicker lubrication filmand better protection of the contacting machine elements.

In another aspect, as the oil operating temperature decreases, theviscosity of a high VI oil will not increase as much as the viscosity ofa low VI oil. This is advantageous because the excessive high viscosityof the low VI oil will decrease the efficiency of the operating machineThus high VI (HVI) oil has performance advantages in both high and lowtemperature operation. VI is determined according to ASTM method D2270-93 [1998]. VI is related to kinematic viscosities measured at 100°C. using ASTM Method D 445-01.

Lubricating Oil Basestocks

A wide range of lubricating oils is known in the art. Lubricating oilsthat are useful in the present disclosure are both natural oils andsynthetic oils. Natural and synthetic oils (or mixtures thereof) can beused unrefined, refined, or rerefined (the latter is also known asreclaimed or reprocessed oil). Unrefined oils are those obtaineddirectly from a natural or synthetic source and used without addedpurification. These include shale oil obtained directly from retortingoperations, petroleum oil obtained directly from primary distillation,and ester oil obtained directly from an esterification process. Refinedoils are similar to the oils discussed for unrefined oils except refinedoils are subjected to one or more purification steps to improve the atleast one lubricating oil property. One skilled in the art is familiarwith many purification processes. These processes include solventextraction, secondary distillation, acid extraction, base extraction,filtration, and percolation. Rerefined oils are obtained by processesanalogous to refined oils but using an oil that has been previously usedas a feed stock.

Groups I, II, III, IV and V are broad categories of base oil stocksdeveloped and defined by the American Petroleum Institute (APIPublication 1509; www.API.org) to create guidelines for lubricant baseoils. Group I basestocks generally have a viscosity index of betweenabout 80 to 120 and contain greater than about 0.03% sulfur and lessthan about 90% saturates. Group II basestocks generally have a viscosityindex of between about 80 to 120, and contain less than or equal toabout 0.03% sulfur and greater than or equal to about 90% saturates.Group III stock generally has a viscosity index greater than 120 andcontains less than or equal to about 0.03% sulfur and greater than about90% saturates. Group IV includes polyalphaolefins (PAO). Group Vbasestocks include basestocks not included in Groups I-IV. The tablebelow summarizes properties of each of these five groups.

Base Oil Properties Saturates Sulfur Viscosity Index Group I <90and/or >0.03% and ≧80 and <120 Group II ≧90 and ≦0.03% and ≧80 and <120Group III ≧90 and ≦0.03% and ≧120 Group IV Includes polyalphaolefins(PAO) products Group V All other base oil stocks not included in GroupsI, II, III or IV

Natural oils include animal oils, vegetable oils (castor oil and lardoil, for example), and mineral oils. Animal and vegetable oilspossessing favorable thermal oxidative stability can be used. Of thenatural oils, mineral oils are preferred. Mineral oils vary widely as totheir crude source, for example, as to whether they are paraffinic,naphthenic, or mixed paraffinic-naphthenic. Oils derived from coal orshale are also useful in the present disclosure. Natural oils vary alsoas to the method used for their production and purification, forexample, their distillation range and whether they are straight run orcracked, hydrorefined, or solvent extracted.

Group II and/or Group III hydroprocessed or hydrocracked basestocks, aswell as synthetic oils such as polyalphaolefins, alkyl aromatics andsynthetic esters, i.e. Group IV and Group V oils are also well knownbasestock oils.

Synthetic oils include hydrocarbon oil such as polymerized andinterpolymerized olefins (polybutylenes, polypropylenes, propyleneisobutylene copolymers, ethylene-olefin copolymers, andethylene-alphaolefin copolymers, for example). Polyalphaolefin (PAO) oilbasestocks, the Group IV API basestocks, are a commonly used synthetichydrocarbon oil. By way of example, PAOs derived from C₈, C₁₀, C₁₂, C₁₄olefins or mixtures thereof may be utilized. See U.S. Pat. Nos.4,956,122; 4,827,064; and 4,827,073, which are incorporated herein byreference in their entirety. Group IV oils, that is, the PAO basestockshave viscosity indices preferably greater than 130, more preferablygreater than 135, still more preferably greater than 140.

Esters in a minor amount may be useful in the lubricating oils of thisdisclosure. Additive solvency and seal compatibility characteristics maybe secured by the use of esters such as the esters of dibasic acids withmonoalkanols and the polyol esters of monocarboxylic acids. Esters ofthe former type include, for example, the esters of dicarboxylic acidssuch as phthalic acid, succinic acid, sebacic acid, fumaric acid, adipicacid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenylmalonic acid, etc., with a variety of alcohols such as butyl alcohol,hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, etc. Specificexamples of these types of esters include dibutyl adipate,di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate,diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecylphthalate, dieicosyl sebacate, etc.

Particularly useful synthetic esters are those which are obtained byreacting one or more polyhydric alcohols, preferably the hinderedpolyols such as the neopentyl polyols; e.g., neopentyl glycol,trimethylol ethane, 2-methyl-2-propyl-1,3-propanediol, trimethylolpropane, pentaerythritol and dipentaerythritol with alkanoic acidscontaining at least about 4 carbon atoms, preferably C₅ to C₃₀ acidssuch as saturated straight chain fatty acids including caprylic acid,capric acids, lauric acid, myristic acid, palmitic acid, stearic acid,arachic acid, and behenic acid, or the corresponding branched chainfatty acids or unsaturated fatty acids such as oleic acid, or mixturesof any of these materials.

Esters should be used in an amount such that the improved wear andcorrosion resistance provided by the lubricating oils of this disclosureare not adversely affected.

Non-conventional or unconventional basestocks and/or base oils includeone or a mixture of basestock(s) and/or base oil(s) derived from: (1)one or more Gas-to-Liquids (GTL) materials, as well as (2) hydrodewaxed,or hydroisomerized/cat (and/or solvent) dewaxed basestock(s) and/or baseoils derived from synthetic wax, natural wax or waxy feeds, mineraland/or non-mineral oil waxy feed stocks such as gas oils, slack waxes(derived from the solvent dewaxing of natural oils, mineral oils orsynthetic oils; e.g., Fischer-Tropsch feed stocks), natural waxes, andwaxy stocks such as gas oils, waxy fuels hydrocracker bottoms, waxyraffinate, hydrocrackate, thermal crackates, foots oil or other mineral,mineral oil, or even non-petroleum oil derived waxy materials such aswaxy materials recovered from coal liquefaction or shale oil, linear orbranched hydrocarbyl compounds with carbon number of about 20 orgreater, preferably about 30 or greater and mixtures of such basestocksand/or base oils.

GTL materials are materials that are derived via one or more synthesis,combination, transformation, rearrangement, and/ordegradation/deconstructive processes from gaseous carbon-containingcompounds, hydrogen-containing compounds and/or elements as feed stockssuch as hydrogen, carbon dioxide, carbon monoxide, water, methane,ethane, ethylene, acetylene, propane, propylene, propyne, butane,butylenes, and butynes. GTL basestocks and/or base oils are GTLmaterials of lubricating viscosity that are generally derived fromhydrocarbons; for example, waxy synthesized hydrocarbons, that arethemselves derived from simpler gaseous carbon-containing compounds,hydrogen-containing compounds and/or elements as feed stocks. GTLbasestock(s) and/or base oil(s) include oils boiling in the lube oilboiling range (1) separated/fractionated from synthesized GTL materialssuch as, for example, by distillation and subsequently subjected to afinal wax processing step which involves either or both of a catalyticdewaxing process, or a solvent dewaxing process, to produce lube oils ofreduced/low pour point; (2) synthesized wax isomerates, comprising, forexample, hydrodewaxed or hydroisomerized cat and/or solvent dewaxedsynthesized wax or waxy hydrocarbons; (3) hydrodewaxed orhydroisomerized cat and/or solvent dewaxed Fischer-Tropsch (F-T)material (i.e., hydrocarbons, waxy hydrocarbons, waxes and possibleanalogous oxygenates); preferably hydrodewaxed orhydroisomerized/followed by cat and/or solvent dewaxing dewaxed F-T waxyhydrocarbons, or hydrodewaxed or hydroisomerized/followed by cat (orsolvent) dewaxing dewaxed, F-T waxes, or mixtures thereof.

GTL basestock(s) and/or base oil(s) derived from GTL materials,especially, hydrodewaxed or hydroisomerized/followed by cat and/orsolvent dewaxed wax or waxy feed, preferably F-T material derivedbasestock(s) and/or base oil(s), are characterized typically as havingkinematic viscosities at 100° C. of from about 2 mm²/s to about 50 mm²/s(ASTM D445). They are further characterized typically as having pourpoints of −5° C. to about −40° C. or lower (ASTM D97). They are alsocharacterized typically as having viscosity indices of about 80 to 140or greater (ASTM D2270).

In addition, the GTL basestock(s) and/or base oil(s) are typicallyhighly paraffinic (>90% saturates), and may contain mixtures ofmonocycloparaffins and multicycloparaffins in combination withnon-cyclic isoparaffins. The ratio of the naphthenic (i.e.,cycloparaffin) content in such combinations varies with the catalyst andtemperature used. Further, GTL basestock(s) and/or base oil(s) typicallyhave very low sulfur and nitrogen content, generally containing lessthan 10 ppm, and more typically less than about 5 ppm of each of theseelements. The sulfur and nitrogen content of GTL basestock(s) and/orbase oil(s) obtained from F-T material, especially F-T wax, isessentially nil. In addition, the absence of phosphorous and aromaticsmake this materially especially suitable for the formulation of low SAPproducts.

The term GTL basestock and/or base oil and/or wax isomerate basestockand/or base oil is to be understood as embracing individual fractions ofsuch materials of wide viscosity range as recovered in the productionprocess, mixtures of two or more of such fractions, as well as mixturesof one or two or more low viscosity fractions with one, two or morehigher viscosity fractions to produce a blend wherein the blend exhibitsa target kinematic viscosity.

The GTL material, from which the GTL basestock(s) and/or base oil(s)is/are derived is preferably an F-T material (i.e., hydrocarbons, waxyhydrocarbons, wax).

Base oils for use in the formulated lubricating oils useful in thepresent disclosure are any of the variety of oils corresponding to APIGroup I, Group II, Group III, Group IV, Group V and Group VI oils andmixtures thereof, preferably API Group II, Group III, Group IV, Group Vand Group VI oils and mixtures thereof, more preferably the Group III toGroup VI base oils due to their exceptional volatility, stability,viscometric and cleanliness features. Minor quantities of Group I stock,such as the amount used to dilute additives for blending into formulatedlube oil products, can be tolerated but should be kept to a minimum,i.e. amounts only associated with their use as diluent/carrier oil foradditives used on an “as received” basis. Even in regard to the Group IIstocks, it is preferred that the Group II stock be in the higher qualityrange associated with that stock, i.e. a Group II stock having aviscosity index in the range 100<VI<120.

In addition, the GTL basestock(s) and/or base oil(s) are typicallyhighly paraffinic (>90% saturates), and may contain mixtures ofmonocycloparaffins and multicycloparaffins in combination withnon-cyclic isoparaffins. The ratio of the naphthenic (i.e.,cycloparaffin) content in such combinations varies with the catalyst andtemperature used. Further, GTL basestock(s) and/or base oil(s) andhydrodewaxed, or hydroisomerized/cat (and/or solvent) dewaxedbasestock(s) and/or base oil(s) typically have very low sulfur andnitrogen content, generally containing less than 10 ppm, and moretypically less than about 5 ppm of each of these elements. The sulfurand nitrogen content of GTL basestock(s) and/or base oil(s) obtainedfrom F-T material, especially F-T wax, is essentially nil. In addition,the absence of phosphorous and aromatics make this material especiallysuitable for the formulation of low sulfur, sulfated ash, and phosphorus(low SAP) products.

The basestock component of the present lubricating oils will typicallybe from 1 to 99 weight percent of the total composition (all proportionsand percentages set out in this specification are by weight unless thecontrary is stated) and more usually in the range of 10 to 99 weightpercent.

Cobasestock Components

Cobasestock components useful in this disclosure include, for example,fluids containing one or more compounds represented by formula (1):R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1)wherein R₁ and R₂ are the same or different and are the residue of anolefin having from about 4 to about 40 carbon atoms; and each R₃ and R₄are the same or different and are an alkyl group having from 1 to about20 carbon atoms; wherein the olefin is selected from the groupconsisting of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and aheteroatom-containing olefin; or fluids containing one or more compoundsrepresented by formula (2):R₅—Si(OR₆)₃  (2)wherein R₁ is the residue of an olefin having from about 4 to about 40carbon atoms; and each R₂ is the same or different and is an alkyl grouphaving from 1 to about 20 carbon atoms; wherein the olefin is selectedfrom the group consisting of an aliphatic olefin, an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin.

The fluids of this disclosure include mixtures. Illustrative mixturesinclude, for example, two or more compounds represented by formula (1);two or more compounds represented by formula (2); and two or morecompounds represented by formula (1) and formula (2).

The fluids of this disclosure have a viscosity (Kv₁₀₀) from about 2 toabout 300 cst at 100° C., and a viscosity index (VI) from about −100 toabout 300. Preferably, the fluids have a viscosity (Kv₁₀₀) from about2.1 to about 250 cst at 100° C., more preferably from 2.2 to 200 cst at100° C., and even more preferably from 2.3 to about 150 cst at 100° C.Preferably, the fluids have a viscosity index (VI) from about −100 toabout 300, more preferably from about 0 to 280, and even more preferablyfrom about 50 to 250. As used herein, viscosity (Kv₁₀₀) is determined byASTM D 445-01, and viscosity index (VI) is determined by ASTM D 2270-93(1998).

The fluids of this disclosure have a Noack volatility of no greater than90 percent, preferably no greater than 80 percent, and more preferablyno greater than about 50 percent. As used herein, Noack volatility isdetermined by ASTM D-5800. In particular, the fluids of this disclosurecan function in engines without volatilization at specific temperatures(e.g., 247-249° C., Noack conditions).

Illustrative R₁, R₂ and R₅ substituents include, for example, theresidue of an aliphatic olefin, an aromatic olefin, a cycloaliphaticolefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, aheteroatom-containing olefin, and the like, as described herein.

Illustrative R₃, R₄ and R₆ substituents include, for example, linear orbranched alkyl groups having from 1 to about 20 carbon atoms, preferablylinear or branched alkyl groups having from 1 to 10 carbon atoms, andmore preferably linear or branched alkyl groups having from 1 to about 8carbon atoms. Illustrative R₃, R₄ and R₆ substituents include, forexample, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, andthe like.

Illustrative compounds of formula (1) and formula (2) are describedherein.

Methods for the production of the alkylated siloxane-containing andalkylated alkoxy silane-containing cobasestock components suitable foruse in the present disclosure are described herein.

The alkylated siloxane-containing and alkylated alkoxy silane-containingcobasestock component is preferably present in an amount sufficient forproviding solubility and dispersancy of polar additives and/or sludge inthe lubricating oil. The alkylated siloxane-containing and alkylatedalkoxy silane-containing cobasestock component is present in thelubricating oils of this disclosure in an amount from 1 to about 99weight percent, preferably from about 5 to about 95 weight percent, andmore preferably from 10 to about 90 weight percent.

Other Additives

The formulated lubricating oil useful in the present disclosure mayadditionally contain one or more of the other commonly used lubricatingoil performance additives including but not limited to dispersants,other detergents, corrosion inhibitors, rust inhibitors, metaldeactivators, other anti-wear agents and/or extreme pressure additives,anti-seizure agents, wax modifiers, viscosity index improvers, viscositymodifiers, fluid-loss additives, seal compatibility agents, otherfriction modifiers, lubricity agents, anti-staining agents, chromophoricagents, defoamants, demulsifiers, emulsifiers, densifiers, wettingagents, gelling agents, tackiness agents, colorants, and others. For areview of many commonly used additives, see Klamann in Lubricants andRelated Products, Verlag Chemie, Deerfield Beach, Fla.; ISBN0-89573-177-0. Reference is also made to “Lubricant Additives Chemistryand Applications” edited by Leslie R. Rudnick, Marcel Dekker, Inc. NewYork, 2003 ISBN: 0-8247-0857-1.

The types and quantities of performance additives used in combinationwith the instant disclosure in lubricant compositions are not limited bythe examples shown herein as illustrations.

Viscosity Improvers

Viscosity improvers (also known as Viscosity Index modifiers, and VIimprovers) increase the viscosity of the oil composition at elevatedtemperatures which increases film thickness, while having limited effecton viscosity at low temperatures.

Suitable viscosity improvers include high molecular weight hydrocarbons,polyesters and viscosity index improver dispersants that function asboth a viscosity index improver and a dispersant. Typical molecularweights of these polymers are between 10,000 to 1,000,000, moretypically about 20,000 to 500,000, and even more typically between about50,000 and 200,000.

Examples of suitable viscosity improvers are polymers and copolymers ofmethacrylate, butadiene, olefins, or alkylated styrenes. Polyisobutyleneis a commonly used viscosity index improver. Another suitable viscosityindex improver is polymethacrylate (copolymers of various chain lengthalkyl methacrylates, for example), some formulations of which also serveas pour point depressants. Other suitable viscosity index improversinclude copolymers of ethylene and propylene, hydrogenated blockcopolymers of styrene and isoprene, and polyacrylates (copolymers ofvarious chain length acrylates, for example). Specific examples includestyrene-isoprene or styrene-butadiene based polymers of 50,000 to200,000 molecular weight.

The amount of viscosity modifier may range from zero to 8 wt %,preferably zero to 4 wt %, more preferably zero to 2 wt % based onactive ingredient and depending on the specific viscosity modifier used.

Antioxidants

Typical antioxidant include phenolic antioxidants, aminic antioxidantsand oil-soluble copper complexes.

The phenolic antioxidants include sulfurized and non-sulfurized phenolicantioxidants. The terms “phenolic type” or “phenolic antioxidant” usedherein includes compounds having one or more than one hydroxyl groupbound to an aromatic ring which may itself be mononuclear, e.g., benzyl,or poly-nuclear, e.g., naphthyl and spiro aromatic compounds. Thus“phenol type” includes phenol per se, catechol, resorcinol,hydroquinone, naphthol, etc., as well as alkyl or alkenyl and sulfurizedalkyl or alkenyl derivatives thereof, and bisphenol type compoundsincluding such bi-phenol compounds linked by alkylene bridges sulfuricbridges or oxygen bridges. Alkyl phenols include mono- and poly-alkyl oralkenyl phenols, the alkyl or alkenyl group containing from about 3-100carbons, preferably 4 to 50 carbons and sulfurized derivatives thereof,the number of alkyl or alkenyl groups present in the aromatic ringranging from 1 to up to the available unsatisfied valences of thearomatic ring remaining after counting the number of hydroxyl groupsbound to the aromatic ring.

Generally, therefore, the phenolic anti-oxidant may be represented bythe general formula:(R)_(x)—Ar—(OH)_(y)where Ar is selected from the group consisting of:

wherein R is a C₃-C₁₀₀ alkyl or alkenyl group, a sulfur substitutedalkyl or alkenyl group, preferably a C₄-C₅₀ alkyl or alkenyl group orsulfur substituted alkyl or alkenyl group, more preferably C₃-C₁₀₀ alkylor sulfur substituted alkyl group, most preferably a C₄-C₅₀ alkyl group,R^(G) is a C₁-C₁₀₀ alkylene or sulfur substituted alkylene group,preferably a C₂-C₅₀ alkylene or sulfur substituted alkylene group, morepreferably a C₂-C₂ alkylene or sulfur substituted alkylene group, y isat least 1 to up to the available valences of Ar, x ranges from 0 to upto the available valances of Ar-y, z ranges from 1 to 10, n ranges from0 to 20, and m is 0 to 4 and p is 0 or 1, preferably y ranges from 1 to3, x ranges from 0 to 3, z ranges from 1 to 4 and n ranges from 0 to 5,and p is 0.

Preferred phenolic antioxidant compounds are the hindered phenolics andphenolic esters which contain a sterically hindered hydroxyl group, andthese include those derivatives of dihydroxy aryl compounds in which thehydroxyl groups are in the o- or p-position to each other. Typicalphenolic antioxidants include the hindered phenols substituted with C₁+alkyl groups and the alkylene coupled derivatives of these hinderedphenols. Examples of phenolic materials of this type 2-t-butyl-4-heptylphenol; 2-t-butyl-4-octyl phenol; 2-t-butyl-4-dodecyl phenol;2,6-di-t-butyl-4-heptyl phenol; 2,6-di-t-butyl-4-dodecyl phenol;2-methyl-6-t-butyl-4-heptyl phenol; 2-methyl-6-t-butyl-4-dodecyl phenol;2,6-di-t-butyl-4 methyl phenol; 2,6-di-t-butyl-4-ethyl phenol; and2,6-di-t-butyl 4 alkoxy phenol; and

Phenolic type antioxidants are well known in the lubricating industryand commercial examples such as Ethanox® 4710, Irganox® 1076, Irganox®L1035, Irganox® 1010, Irganox® L109, Irganox® L118, Irganox® L135 andthe like are familiar to those skilled in the art. The above ispresented only by way of exemplification, not limitation on the type ofphenolic antioxidants which can be used.

The phenolic antioxidant can be employed in an amount in the range ofabout 0.1 to 3 wt %, preferably 1 to 3 wt %, more preferably 1.5 to 3 wt% on an active ingredient basis.

Aromatic amine antioxidants include phenyl-α-naphthyl amine which isdescribed by the following molecular structure:

wherein R^(z) is hydrogen or a C₁ to C₁₄ linear or C₃ to C₁₄ branchedalkyl group, preferably C₁ to C₁₀ linear or C₃ to C₁₀ branched alkylgroup, more preferably linear or branched C₆ to C₈ and n is an integerranging from 1 to 5 preferably 1. A particular example is Irganox L06.

Other aromatic amine anti-oxidants include other alkylated andnon-alkylated aromatic amines such as aromatic monoamines of the formulaR⁸R⁹R¹⁰N where R⁸ is an aliphatic, aromatic or substituted aromaticgroup, R⁹ is an aromatic or a substituted aromatic group, and R¹⁰ is H,alkyl, aryl or R¹¹S(O)_(x)R¹² where R¹¹ is an alkylene, alkenylene, oraralkylene group, R¹² is a higher alkyl group, or an alkenyl, aryl, oralkaryl group, and x is 0, 1 or 2. The aliphatic group R⁸ may containfrom 1 to about 20 carbon atoms, and preferably contains from about 6 to12 carbon atoms. The aliphatic group is a saturated aliphatic group.Preferably, both R⁸ and R⁹ are aromatic or substituted aromatic groups,and the aromatic group may be a fused ring aromatic group such asnaphthyl. Aromatic groups R⁸ and R⁹ may be joined together with othergroups such as S.

Typical aromatic amines antioxidants have alkyl substituent groups of atleast about 6 carbon atoms. Examples of aliphatic groups include hexyl,heptyl, octyl, nonyl, and decyl. Generally, the aliphatic groups willnot contain more than 14 carbon atoms. The general types of such otheradditional amine antioxidants which may be present includediphenylamines, phenothiazines, imidodibenzyls and diphenyl phenylenediamines. Mixtures of two or more of such other additional aromaticamines may also be present. Polymeric amine antioxidants can also beused.

Another class of antioxidant used in lubricating oil compositions andwhich may also be present are oil-soluble copper compounds. Anyoil-soluble suitable copper compound may be blended into the lubricatingoil. Examples of suitable copper antioxidants include copperdihydrocarbyl thio- or dithiophosphates and copper salts of carboxylicacid (naturally occurring or synthetic). Other suitable copper saltsinclude copper dithiacarbamates, sulphonates, phenates, andacetylacetonates. Basic, neutral, or acidic copper Cu(I) and or Cu(II)salts derived from alkenyl succinic acids or anhydrides are known to beparticularly useful.

Such antioxidants may be used individually or as mixtures of one or moretypes of antioxidants, the total amount employed being an amount ofabout 0.50 to 5 wt %, preferably about 0.75 to 3 wt % (on an as-receivedbasis).

Detergents

In addition to the alkali or alkaline earth metal salicylate detergentwhich is an essential component in the present disclosure, otherdetergents may also be present. While such other detergents can bepresent, it is preferred that the amount employed be such as to notinterfere with the synergistic effect attributable to the presence ofthe salicylate. Therefore, most preferably such other detergents are notemployed.

If such additional detergents are present, they can include alkali andalkaline earth metal phenates, sulfonates, carboxylates, phosphonatesand mixtures thereof. These supplemental detergents can have total basenumber (TBN) ranging from neutral to highly overbased, i.e. TBN of 0 toover 500, preferably 2 to 400, more preferably 5 to 300, and they can bepresent either individually or in combination with each other in anamount in the range of from 0 to 10 wt %, preferably 0.5 to 5 wt %(active ingredient) based on the total weight of the formulatedlubricating oil. As previously stated, however, it is preferred thatsuch other detergent not be present in the formulation.

Such additional other detergents include by way of example and notlimitation calcium phenates, calcium sulfonates, magnesium phenates,magnesium sulfonates and other related components (including borateddetergents).

Dispersants

During engine operation, oil-insoluble oxidation byproducts areproduced. Dispersants help keep these byproducts in solution, thusdiminishing their deposition on metal surfaces. Dispersants may beashless or ash-forming in nature. Preferably, the dispersant is ashless.So called ashless dispersants are organic materials that formsubstantially no ash upon combustion. For example, non-metal-containingor borated metal-free dispersants are considered ashless. In contrast,metal-containing detergents discussed above form ash upon combustion.

Suitable dispersants typically contain a polar group attached to arelatively high molecular weight hydrocarbon chain. The polar grouptypically contains at least one element of nitrogen, oxygen, orphosphorus. Typical hydrocarbon chains contain 50 to 400 carbon atoms.

A particularly useful class of dispersants are the alkenylsuccinicderivatives, typically produced by the reaction of a long chainsubstituted alkenyl succinic compound, usually a substituted succinicanhydride, with a polyhydroxy or polyamino compound. The long chaingroup constituting the oleophilic portion of the molecule which conferssolubility in the oil, is normally a polyisobutylene group. Manyexamples of this type of dispersant are well known commercially and inthe literature. Exemplary patents describing such dispersants are U.S.Pat. Nos. 3,172,892; 3,219,666; 3,316,177 and 4,234,435. Other types ofdispersants are described in U.S. Pat. Nos. 3,036,003; and 5,705,458.

Hydrocarbyl-substituted succinic acid compounds are popular dispersants.In particular, succinimide, succinate esters, or succinate ester amidesprepared by the reaction of a hydrocarbon-substituted succinic acidcompound preferably having at least 50 carbon atoms in the hydrocarbonsubstituent, with at least one equivalent of an alkylene amine areparticularly useful.

Succinimides are formed by the condensation reaction between alkenylsuccinic anhydrides and amines. Molar ratios can vary depending on theamine or polyamine. For example, the molar ratio of alkenyl succinicanhydride to TEPA can vary from 1:1 to about 5:1.

Succinate esters are formed by the condensation reaction between alkenylsuccinic anhydrides and alcohols or polyols. Molar ratios can varydepending on the alcohol or polyol used. For example, the condensationproduct of an alkenyl succinic anhydride and pentaerythritol is a usefuldispersant.

Succinate ester amides are formed by condensation reaction betweenalkenyl succinic anhydrides and alkanol amines. For example, suitablealkanol amines include ethoxylated polyalkylpolyamines, propoxylatedpolyalkylpolyamines and polyalkenylpolyamines such as polyethylenepolyamines. One example is propoxylated hexamethylenediamine.

The molecular weight of the alkenyl succinic anhydrides will typicallyrange between 800 and 2,500. The above products can be post-reacted withvarious reagents such as sulfur, oxygen, formaldehyde, carboxylic acidssuch as oleic acid, and boron compounds such as borate esters or highlyborated dispersants. The dispersants can be borated with from about 0.1to about 5 moles of boron per mole of dispersant reaction product.

Mannich base dispersants are made from the reaction of alkylphenols,formaldehyde, and amines. Process aids and catalysts, such as oleic acidand sulfonic acids, can also be part of the reaction mixture. Molecularweights of the alkylphenols range from 800 to 2,500.

Typical high molecular weight aliphatic acid modified Mannichcondensation products can be prepared from high molecular weightalkyl-substituted hydroxyaromatics or HN(R)₂ group-containing reactants.

Examples of high molecular weight alkyl-substituted hydroxyaromaticcompounds are polypropylphenol, polybutylphenol, and otherpolyalkylphenols. These polyalkylphenols can be obtained by thealkylation, in the presence of an alkylating catalyst, such as BF₃, ofphenol with high molecular weight polypropylene, polybutylene, and otherpolyalkylene compounds to give alkyl substituents on the benzene ring ofphenol having an average 600-100,000 molecular weight.

Examples of HN(R)₂ group-containing reactants are alkylene polyamines,principally polyethylene polyamines. Other representative organiccompounds containing at least one HN(R)₂ group suitable for use in thepreparation of Mannich condensation products are well known and includethe mono- and diamino alkanes and their substituted analogs, e.g.,ethylamine and diethanol amine; aromatic diamines, e.g., phenylenediamine, diamino naphthalenes; heterocyclic amines, e.g., morpholine,pyrrole, pyrrolidine, imidazole, imidazolidine, and piperidine; melamineand their substituted analogs.

Examples of alkylene polyamine reactants include ethylenediamine,diethylene triamine, triethylene tetraamine, tetraethylene pentaamine,pentaethylene hexamine, hexaethylene heptaamine, heptaethyleneoctaamine, octaethylene nonaamine, nonaethylene decamine, anddecaethylene undecamine and mixture of such amines having nitrogencontents corresponding to the alkylene polyamines, in the formulaH₂N—(Z—NH—)_(n)H, mentioned before, Z is a divalent ethylene and n is 1to 10 of the foregoing formula. Corresponding propylene polyamines suchas propylene diamine and di-, tri-, tetra-, pentapropylene tri-, tetra-,penta- and hexaamines are also suitable reactants. The alkylenepolyamines are usually obtained by the reaction of ammonia and dihaloalkanes, such as dichloro alkanes. Thus the alkylene polyamines obtainedfrom the reaction of 2 to 11 moles of ammonia with 1 to 10 moles ofdichloroalkanes having 2 to 6 carbon atoms and the chlorines ondifferent carbons are suitable alkylene polyamine reactants.

Aldehyde reactants useful in the preparation of the high molecularproducts useful in this disclosure include the aliphatic aldehydes suchas formaldehyde (also as paraformaldehyde and formalin), acetaldehydeand aldol (β-hydroxybutyraldehyde). Formaldehyde or aformaldehyde-yielding reactant is preferred.

Preferred dispersants include borated and non-borated succinimides,including those derivatives from mono-succinimides, bis-succinimides,and/or mixtures of mono- and bis-succinimides, wherein the hydrocarbylsuccinimide is derived from a hydrocarbylene group such aspolyisobutylene having a Mn of from about 500 to about 5000 or a mixtureof such hydrocarbylene groups. Other preferred dispersants includesuccinic acid-esters and amides, alkylphenol-polyamine-coupled Mannichadducts, their capped derivatives, and other related components. Suchadditives may be used in an amount of about 0.1 to 20 wt %, preferablyabout 0.1 to 8 wt %, more preferably 1 to 6 wt % (on an as-receivedbasis) based on the weight of the total lubricant.

Pour Point Depressants

Conventional pour point depressants (also known as lube oil flowimprovers) may also be present. Pour point depressant may be added tolower the minimum temperature at which the fluid will flow or can bepoured. Examples of suitable pour point depressants include alkylatednaphthalenes polymethacrylates, polyacrylates, polyarylamides,condensation products of haloparaffin waxes and aromatic compounds,vinyl carboxylate polymers, and terpolymers of dialkylfumarates, vinylesters of fatty acids and allyl vinyl ethers. Such additives may be usedin amount of about 0.0 to 0.5 wt %, preferably about 0 to 0.3 wt %, morepreferably about 0.001 to 0.1 wt % on an as-received basis.

Corrosion Inhibitors/Metal Deactivators

Corrosion inhibitors are used to reduce the degradation of metallicparts that are in contact with the lubricating oil composition. Suitablecorrosion inhibitors include aryl thiazines, alkyl substituteddimercapto thiodiazoles thiadiazoles and mixtures thereof. Suchadditives may be used in an amount of about 0.01 to 5 wt %, preferablyabout 0.01 to 1.5 wt %, more preferably about 0.01 to 0.2 wt %, stillmore preferably about 0.01 to 0.1 wt % (on an as-received basis) basedon the total weight of the lubricating oil composition.

Seal Compatibility Additives

Seal compatibility agents help to swell elastomeric seals by causing achemical reaction in the fluid or physical change in the elastomer.Suitable seal compatibility agents for lubricating oils include organicphosphates, aromatic esters, aromatic hydrocarbons, esters (butylbenzylphthalate, for example), and polybutenyl succinic anhydride andsulfolane-type seal swell agents such as Lubrizol 730-type seal swelladditives. Such additives may be used in an amount of about 0.01 to 3 wt%, preferably about 0.01 to 2 wt % on an as-received basis.

Anti-Foam Agents

Anti-foam agents may advantageously be added to lubricant compositions.These agents retard the formation of stable foams. Silicones and organicpolymers are typical anti-foam agents. For example, polysiloxanes, suchas silicon oil or polydimethyl siloxane, provide antifoam properties.Anti-foam agents are commercially available and may be used inconventional minor amounts along with other additives such asdemulsifiers; usually the amount of these additives combined is lessthan 1 percent, preferably 0.001 to about 0.5 wt %, more preferablyabout 0.001 to about 0.2 wt %, still more preferably about 0.0001 to0.15 wt % (on an as-received basis) based on the total weight of thelubricating oil composition.

Inhibitors and Antirust Additives

Antirust additives (or corrosion inhibitors) are additives that protectlubricated metal surfaces against chemical attack by water or othercontaminants. One type of anti-rust additive is a polar compound thatwets the metal surface preferentially, protecting it with a film of oil.Another type of anti-rust additive absorbs water by incorporating it ina water-in-oil emulsion so that only the oil touches the surface. Yetanother type of anti-rust additive chemically adheres to the metal toproduce a non-reactive surface. Examples of suitable additives includezinc dithiophosphates, metal phenolates, basic metal sulfonates, fattyacids and amines. Such additives may be used in an amount of about 0.01to 5 wt %, preferably about 0.01 to 1.5 wt % on an as-received basis.

In addition to the ZDDP antiwear additives which are essentialcomponents of the present disclosure, other antiwear additives can bepresent, including zinc dithiocarbamates, molybdenumdialkyldithiophosphates, molybdenum dithiocarbamates, other organomolybdenum-nitrogen complexes, sulfurized olefins, etc.

The term “organo molybdenum-nitrogen complexes” embraces the organomolybdenum-nitrogen complexes described in U.S. Pat. No. 4,889,647. Thecomplexes are reaction products of a fatty oil, dithanolamine and amolybdenum source. Specific chemical structures have not been assignedto the complexes. U.S. Pat. No. 4,889,647 reports an infrared spectrumfor a typical reaction product of that disclosure; the spectrumidentifies an ester carbonyl band at 1740 cm⁻¹ and an amide carbonylband at 1620 cm⁻¹. The fatty oils are glyceryl esters of higher fattyacids containing at least 12 carbon atoms up to 22 carbon atoms or more.The molybdenum source is an oxygen-containing compound such as ammoniummolybdates, molybdenum oxides and mixtures.

Other organo molybdenum complexes which can be used in the presentdisclosure are tri-nuclear molybdenum-sulfur compounds described in EP 1040 115 and WO 99/31113 and the molybdenum complexes described in U.S.Pat. No. 4,978,464.

In the above detailed description, the specific embodiments of thisdisclosure have been described in connection with its preferredembodiments. However, to the extent that the above description isspecific to a particular embodiment or a particular use of thisdisclosure, this is intended to be illustrative only and merely providesa concise description of the exemplary embodiments. Accordingly, thedisclosure is not limited to the specific embodiments described above,but rather, the disclosure includes all alternatives, modifications, andequivalents falling within the true scope of the appended claims.Various modifications and variations of this disclosure will be obviousto a worker skilled in the art and it is to be understood that suchmodifications and variations are to be included within the purview ofthis application and the spirit and scope of the claims.

EXAMPLES Example 1 Synthesis of 1,3-didecyl-1,1,3,3-tetramethyldisiloxane

1-Decene (13.1 grams, 0.0931 mol), 1,1,3,3-tetramethyldisiloxane (2.50grams, 0.00186 mol) and 10 milligrams PtO₂ were charged in a 25milliliter thick glass reactor. The reaction mixture was heated at 80°C. for 12 hours. The mixture was cooled to room temperature, saturatedwith air by bubbling air through the mixture for 30 seconds and then themixture was heated to a temperature 85° C. for 2 hours. After coolingdown to room temperature the PtO₂ catalyst removed by filtration andexcess of unreacted 1-decene by a rotary evaporator and high boilingcomponents with vacuum oven at 180° C. with high vacuum for 1 hour. Thefinal product yield was 7.7 grams (yield 90%). The product IR and ¹H NMRanalysis (FIG. 1) suggests the formation of alkyl disiloxane. IR: neat(cm⁻¹): 2921, 2850, 2305, 2165, 1715, 1519, 1377, 1303, 720. ¹H NMR(CDCl₃): δ 1.24 (m, 32H, —CH₂—), 0.86 (t, 6H, —CH₃), 0.47 (t, 4H,—SiCH₂—), 0.00 (s, 12H, Si—CH₃). FIG. 1 shows the ¹HNMR spectra of1,3-didecyl-1,1,3,3-tetrameyhyl disiloxane (bottom spectrum, 26232-71)and 1-decene starting olefin.

Example 2 Synthesis of 1,3-didodecyl-1,1,3,3-tetramethyl disiloxane

1-Dodecene (15.6 grams, 0.0931 mol), 1,1,3,3-tetramethyldisiloxane (2.50grams, 0.00186 mol) and 10 milligrams PtO₂ were charged in a 25milliliter thick glass reactor. The reaction mixture was heated at 80°C. for 12 hours. The mixture was cooled to room temperature, saturatedwith air by bubbling air through the mixture for 30 seconds and then themixture was heated at a temperature of 85° C. for 18 hours. Aftercooling down to room temperature the PtO₂ catalyst was removed byfiltration and excess of unreacted 1-dodecene by a rotary evaporator andhigh boiling components with vacuum oven at 180° C. with high vacuum for1 hour. The final product was yielded 8.5 grams (yield 97%). The productIR and ¹H NMR analysis (FIG. 2) suggests the formation of alkyldisiloxane. IR: neat (cm⁻¹): 2956, 2923, 2853, 1467, 1409, 1378, 1252,1060, 840, 795, 721, 704. ¹H NMR (CDCl₃): δ 1.23 (m, 40H, —CH₂—), 0.86(t, 6H, —CH₃), 0.47 (t, 4H, —SiCH₂—), 0.00 (s, 12H, Si—CH₃). FIG. 2shows the ¹HNMR spectra of 1,3-didodecyl-1,1,3,3-tetrameyhyl disiloxane(bottom spectrum, 26232-75) and 1-dodecene starting olefin.

Example 3 Synthesis of 1,3-di(2-hexyldecyl)-1,1,3,3-tetramethyldisiloxane

C₁₆ dimer (16.6 grams, 0.0744 mol), 1,1,3,3-tetramethyldisiloxane (2.50grams, 0.00186 mol) and 20 milligrams PtO₂ were charged in a 25milliliter thick glass reactor. The reaction mixture was heated at 115°C. for 12 hours. The mixture was cooled to room temperature, saturatedwith air by bubbling air through the mixture for 30 seconds and then themixture was heated at a temperature of 115° C. for 18 hours. Aftercooling down to room temperature, the PtO₂ catalyst was removed byfiltration and excess of unreacted C₁₆ dimer with vacuum oven at 200° C.with high vacuum for 1.5 hours. The final product yielded 9.0 grams(97%). The product IR and ¹H NMR analysis (FIG. 3) suggests theformation of alkyl disiloxane. IR: neat (cm⁻¹): 2956, 2854, 2923, 1467,1378, 1252, 1054, 839, 804, 722. ¹H NMR (CDCl₃): δ 1.22 (m, 48H, —CH₂—),0.86 (t, 12H, —CH₃), 0.47 (d, 4H, —SiCH₂—), 0.00 (s, 12H, Si—CH₃). FIG.3 shows the ¹HNMR spectra of 1,3-di(2-hexyldecyl)-1,1,3,3-tetrameyhyldisiloxane (bottom spectrum, 26232-77) and C₁₆-dimer olefin.

Example 4 Synthesis of Trimethoxy (Octadecyl) Silane

The hydrosilylation reaction of 1-octadecene and trimethoxysilane iscarried out using hexachloro-platinic acid catalyst in 2-propyl alcohol,H₂[PtCl₆].6H₂O. The mole ratio of 1.5 mole equivalent 1-octadecene, 1.0mole equivalent trimethoxysilane and 5×10⁻⁵ mole equivalentH₂[PtCl₆].6H₂O in 2-propanol is initiated at 100-120° C. temperaturesunder moisture and oxygen free inert conditions. After the reaction, thereaction mixture is cooled down to room temperature and the catalyst isremoved by filtration. The excess of unreacted 1-ocatadecene is removedby distillation under vacuum. The final product is qualitativelyyielded. The NMR and FT-IR show the formation of trimethoxy (octadecyl)silane.

Example 5 Lubricant Properties of Basestocks

The kinematic viscosity (Kv) of the liquid products was measured usingASTM standards D-445 and reported at temperatures of 100° C. (Kv at 100°C.) or 40° C. (Kv at 40° C.). The viscosity index (VI) was measuredaccording to ASTM standard D-2270 using the measured kinematicviscosities for each product. The product volatility was measured usingthermogravimetric analysis (TGA Noack). The lube properties wereevaluated and the data are reported in Table 1 below.

The fluids listed in Table 1 were evaluated as synthetic basestocks andfound to have good lubricant properties. These fluids can be used aslubricant basestocks and co-basestocks. These fluids have lowviscosities, lower volatility and very high viscosity index. Forexample, the fluid of the Example 2 with KV₁₀₀ of 2.57 cSt hasexceptionally high VI of 211, while TGA volatility is comparable toPAO4. All these synthetic basestocks have excellent viscosity index. Therelative volatility of the basestocks along with PAO2 and PAO4 weremeasured using TGA Noack test. The TGA Noack data of the fluids ofExamples 1-4 show that they have relatively low volatility compared tohydrocarbon fluids like PAO2 and PAO4. FIG. 4 shows the kinematicviscosity at 100° C. (x-axis) and TGA (Noack) (y-axis) of PAO2, PAO4 andsynthetic fluids of Examples 1-4.

TABLE 1 Basestock # Kv₁₀₀ ° C. Kv₄₀ ° C. VI TGA Noack Example 1 2.105.75 205 34.62 Example 2 2.57 8.66 211 13.52 Example 3 3.28 12.10 14713.62 Example 4 2.30 6.70 184 39.63 PAO2 1.7 5 — 99.73 PAO4 4.10 19.00126 13.45

All patents and patent applications, test procedures (such as ASTMmethods, UL methods, and the like), and other documents cited herein arefully incorporated by reference to the extent such disclosure is notinconsistent with this disclosure and for all jurisdictions in whichsuch incorporation is permitted.

When numerical lower limits and numerical upper limits are listedherein, ranges from any lower limit to any upper limit are contemplated.While the illustrative embodiments of the disclosure have been describedwith particularity, it will be understood that various othermodifications will be apparent to and can be readily made by thoseskilled in the art without departing from the spirit and scope of thedisclosure. Accordingly, it is not intended that the scope of the claimsappended hereto be limited to the examples and descriptions set forthherein but rather that the claims be construed as encompassing all thefeatures of patentable novelty which reside in the present disclosure,including all features which would be treated as equivalents thereof bythose skilled in the art to which the disclosure pertains.

The present disclosure has been described above with reference tonumerous embodiments and specific examples. Many variations will suggestthemselves to those skilled in this art in light of the above detaileddescription. All such obvious variations are within the full intendedscope of the appended claims.

What is claimed is:
 1. A composition comprising one or more compoundsrepresented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1) wherein R₁ and R₂ are the same or differentand are the saturated residue of an olefin having from about 4 to about40 carbon atoms; and each R₃ and R₄ are the same or different and are analkyl group having from 1 to about 20 carbon atoms; wherein the olefinis selected from the group consisting of an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin; and wherein thecomposition has a viscosity (Kv₁₀₀) from about 2 to about 300 cst at100° C., and a viscosity index (VI) from about −100 to about
 300. 2. Thecomposition of claim 1 wherein: the aromatic olefin is selected from2,4-dimethylstyrene, 2,5-dimethylstyrene, 4-tert-butyl styrene,4-tert-butoxystyrene, 3,4-dimethoxystyrene, 4-acetoxystyrene,1,3-diisopropenylbenzene, 4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene,4-fluorostyrene, 1-(trifluoromethyl)-4-vinylbenzene,4-[N-(methylaminoethyl)aminomethyl]styrene,4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol,((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene,2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methylstyrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene,2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene,1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene,1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole,N-vinylphthalimide, and 4-(trifluoromethyl)styrene.
 3. The compositionof claim 1 wherein: the cycloaliphatic olefin is selected fromvinylcyclopentane, vinylcylcohexane, cyclopentene, cyclohexene,cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclododecene,cyclotetradecene, cyclohexadecene, cyclooctadecene, allylcyclohexane,1,2,4-trivinylcyclohexane, and 5-vinyl-2-norbornene.
 4. The compositionof claim 1 wherein: the vinyl ether is selected from ethyl vinyl ether,propyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether,2-ethylhexyl vinyl ether, dodecyl vinyl ether, tetraethylene glycolmethyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether,isooctyl vinyl ether, t-butyl vinyl ether, phenyl vinyl ether,cyclohexyl vinyl ether, 2,2,2-trifluoroethyl vinyl ether, 1,4-butanedioldivinyl ether, di(ethylene glycol) divinyl ether, tri(ethylene glycol)divinyl ether, 1,4-cyclohexanedimethanol divinyl ether,bis[4-(vinyloxy)butyl] isophthalate, bis[4-(vinyloxy)butyl] succinate,diethyl vinyl orthoformate, di(ethylene glycol) vinyl ether, ethyleneglycol vinyl ether, and 1,4-butanediol vinyl ether.
 5. The compositionof claim 1 wherein: the acrylate is selected from methyl acrylate, ethylacrylate, hexyl acrylate, isooctyl acrylate, isodecyl acrylate, laurylacrylate, octadecyl acrylate, di(ethylene glycol) 2-ethylhexyl etheracrylate, di(ethylene glycol) ethyl ether acrylate, ethylene glycolphenyl ether acrylate, 2-ethylhexyl acrylate, butyl acrylate, isobornylacrylate, ethylene glycol methyl ether acrylate, 2-(dimethylamino)ethylacrylate, 2-(diethylamino)ethyl acrylate, 3-(dimethylamino)propylacrylate, pentafluorophenyl acrylate, 1,6-hexanediol diacrylate,trimethylolpropane triacrylate, 4-acetoxyphenethyl acrylate,4-allyloxy-2-hydroxybenzophenone, 2-(4-benzoyl-3-hydroxyphenoxy)ethylacrylate, 4-acryloylmorpholine, 4-tert-butylcyclohexyl acrylate,tetrahydrofurfutyl acrylate, 3,5,5-trimethylhexyl acrylate,di(trimethylolpropane) tetraacrylate,tris[2-(acryloyloxy)ethyl]isocyanurate, pentaerythritol tetraacrylate,1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione,1,3,5-triacryloylhexahydro-1,3,5-triazine,1,1,1,3,3,3-hexafluoroisopropyl acrylate, 9H-carbazole-9-ethyl acrylate,and 2-hydroxypropyl 2-(methacryloyloxy)ethyl phthalate.
 6. Thecomposition of claim 1 wherein: the methacrylate is selected from methylmethacrylate, butyl methacrylate, tert-butyl methacrylate, hexylmethacrylate, 2-ethylhexyl methacrylate, 2-(dimethylamino)ethylmethacrylate, 2-(diethylamino)ethyl methacrylate, di(ethylene glycol)methyl ether methacrylate, lauryl methacrylate, stearyl methacrylate,isobornyl methacrylate, ethylene glycol phenyl ether methacrylate,phenyl methacrylate, cyclohexyl methacrylate, allyl methacrylate, vinylmethacrylate, benzyl methacrylate, 1,6-hexanediol dimethacrylate,bisphenol A dimethacrylate, bisphenol A glycerolate dimethacrylate,2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl] ethyl methacrylate,cyclohexyl methacrylate, tetrahydrofurfutyl methacrylate,2-(tert-butylamino)ethyl methacrylate, 2-(diisopropylamino)ethylmethacrylate, 2-N-morpholinoethyl methacrylate, 9H-carbazole-9-ethylmethacrylate, 1-naphthyl methacrylate, pentafluorophenyl methacrylate,1-pyrenemethayl methacrylate, TEMPO methacrylate, andN-(triphenylmethyl)methacrylamide.
 7. The composition of claim 1wherein: the vinyl ester is selected from vinyl acetate, vinylpropionate, vinyl valerate, vinyl butyrate, vinyl decanoate, vinylstearate, vinyl cinnamate, allyl butyrate, vinyl pivalate, vinylbenzoate, vinyl 4-t-butylbenzoate, and allyl cinnamate.
 8. Thecomposition of claim 1 wherein: the heteroatom-containing olefin isselected from N-methyl-N-vinylacetamide, N,N-dimethylacrylamide,4-vinylpyridine, 2-vinylpyridine, 1-vinyl-2-pyrrolidinone,1-vinyl-1,2,4-triazole, 1-vinylimidazole, N-vinylcaprolactone,4-acryloylmorpholine, 5-vinyluracil, 4-acryloylmorpholine,N,N-dimethylacrylamide, 2-vinyl-1,3-dioxolane, acrolein diethyl acetal,acrolein dimethyl acetal, 4-vinyl-1,3-dioxolane-2-one, vinylbenzoicacid, 1-vinylbenzyl alcohol, vinyl trifluoroacetate, 1-vinylcyclohexanole, vinyloxy trimethylsilane, vinyltrimethylsilane, allyltrimethylsilane, triphenyl(vinyl)silane, and 2-isopropenyl-2-oxazoline.9. A process for preparing a composition comprising one or morecompounds represented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1) wherein R₁ and R₂ are the same or differentand are the saturated residue of an olefin having from about 4 to about40 carbon atoms; and each R₃ and R₄ are the same or different and are analkyl group having from 1 to about 20 carbon atoms; wherein said processcomprises reacting an alkyl siloxane with an olefin, in the presence ofa catalyst, under reaction conditions sufficient to produce saidcomposition; wherein the alkyl siloxane has from about 4 to about 20carbon atoms; and the olefin is selected from the group consisting of anaromatic olefin, a cycloaliphatic olefin, a vinyl ether, an acrylate, amethacrylate, a vinyl ester, and a heteroatom-containing olefin; andwherein the composition has a viscosity (Kv₁₀₀) from about 2 to about300 cst at 100° C., and a viscosity index (VI) from about −100 to about300.
 10. The process of claim 9 wherein the alkyl siloxane comprises1,1,3,3-tetramethyldisiloxane, hexaethoxydisiloxane,1,3-didecyl-1,1,3,3-tetramethyl disiloxane,1,3-didodecyl-1,1,3,3-tetramethyl disiloxane,3-di(2-hexyldecyl)-1,1,3,3-tetramethyl disiloxane,1,3-bis(3-(2-hydroxyethyoxy)propyl)tetramethyldisiloxane,1,3-bis(hydroxypropyl)tetramethyldisiloxane,bis(methoxytriethyleneoxypropyl)tetramethyldisiloxane,1,3-bis(trimethylsiloxy)1,3-dimethyldisiloxane,1,3-bis(3-hydroxyisobutyl)tetramethyldisiloxane, or1,3-diallyltetramethyldisiloxane.
 11. The process of claim 9 wherein:the aromatic olefin is selected from 2,4-dimethylstyrene,2,5-dimethylstyrene, 4-tert-butyl styrene, 4-tert-butoxystyrene,3,4-dimethoxystyrene, 4-acetoxystyrene, 1,3-diisopropenylbenzene,4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene, 4-fluorostyrene,1-(trifluoromethyl)-4-vinylbenzene,4-[N-(methylaminoethyl)aminomethyl]styrene,4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol,((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene,2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methylstyrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene,2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene,1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene,1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole,N-vinylphthalimide, and 4-(trifluoromethyl)styrene.
 12. The process ofclaim 9 wherein: the cycloaliphatic olefin is selected fromvinylcyclopentane, vinylcylcohexane, cyclopentene, cyclohexene,cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclododecene,cyclotetradecene, cyclohexadecene, cyclooctadecene, allylcyclohexane,1,2,4-trivinylcyclohexane, and 5-vinyl-2-norbornene.
 13. The process ofclaim 9 wherein: the vinyl ether is selected from ethyl vinyl ether,propyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether,2-ethylhexyl vinyl ether, dodecyl vinyl ether, tetraethylene glycolmethyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether,isooctyl vinyl ether, t-butyl vinyl ether, phenyl vinyl ether,cyclohexyl vinyl ether, 2,2,2-trifluoroethyl vinyl ether, 1,4-butanedioldivinyl ether, di(ethylene glycol) divinyl ether, tri(ethylene glycol)divinyl ether, 1,4-cyclohexanedimethanol divinyl ether,bis[4-(vinyloxy)butyl] isophthalate, bis[4-(vinyloxy)butyl] succinate,diethyl vinyl orthoformate, di(ethylene glycol) vinyl ether, ethyleneglycol vinyl ether, and 1,4-butanediol vinyl ether.
 14. The process ofclaim 9 wherein: the acrylate is selected from methyl acrylate, ethylacrylate, hexyl acrylate, isooctyl acrylate, isodecyl acrylate, laurylacrylate, octadecyl acrylate, di(ethylene glycol) 2-ethylhexyl etheracrylate, di(ethylene glycol) ethyl ether acrylate, ethylene glycolphenyl ether acrylate, 2-ethylhexyl acrylate, butyl acrylate, isobornylacrylate, ethylene glycol methyl ether acrylate, 2-(dimethylamino)ethylacrylate, 2-(diethylamino)ethyl acrylate, 3-(dimethylamino)propylacrylate, pentafluorophenyl acrylate, 1,6-hexanediol diacrylate,trimethylolpropane triacrylate, 4-acetoxyphenethyl acrylate,4-allyloxy-2-hydroxybenzophenone, 2-(4-benzoyl-3-hydroxyphenoxy)ethylacrylate, 4-acryloylmorpholine, 4-tert-butylcyclohexyl acrylate,tetrahydrofurfutyl acrylate, 3,5,5-trimethylhexyl acrylate,di(trimethylolpropane) tetraacrylate,tris[2-(acryloyloxy)ethyl]isocyanurate, pentaerythritol tetraacrylate,1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione,1,3,5-triacryloylhexahydro-1,3,5-triazine,1,1,1,3,3,3-hexafluoroisopropyl acrylate, 9H-carbazole-9-ethyl acrylate,and 2-hydroxypropyl 2-(methacryloyloxy)ethyl phthalate.
 15. The processof claim 9 wherein: the methacrylate is selected from methylmethacrylate, butyl methacrylate, tert-butyl methacrylate, hexylmethacrylate, 2-ethylhexyl methacrylate, 2-(dimethylamino)ethylmethacrylate, 2-(diethylamino)ethyl methacrylate, di(ethylene glycol)methyl ether methacrylate, lauryl methacrylate, stearyl methacrylate,isobornyl methacrylate, ethylene glycol phenyl ether methacrylate,phenyl methacrylate, cyclohexyl methacrylate, allyl methacrylate, vinylmethacrylate, benzyl methacrylate, 1,6-hexanediol dimethacrylate,bisphenol A dimethacrylate, bisphenol A glycerolate dimethacrylate,2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl] ethyl methacrylate,cyclohexyl methacrylate, tetrahydrofurfutyl methacrylate,2-(tert-butylamino)ethyl methacrylate, 2-(diisopropylamino)ethylmethacrylate, 2-N-morpholinoethyl methacrylate, 9H-carbazole-9-ethylmethacrylate, 1-naphthyl methacrylate, pentafluorophenyl methacrylate,1-pyrenemethayl methacrylate, TEMPO methacrylate, andN-(triphenylmethyl)methacrylamide.
 16. The process of claim 9 wherein:the vinyl ester is selected from vinyl acetate, vinyl propionate, vinylvalerate, vinyl butyrate, vinyl decanoate, vinyl stearate, vinylcinnamate, allyl butyrate, vinyl pivalate, vinyl benzoate, vinyl4-t-butylbenzoate, and allyl cinnamate.
 17. The process of claim 9wherein: the heteroatom-containing olefin is selected fromN-methyl-N-vinylacetamide, N,N-dimethylacrylamide, 4-vinylpyridine,2-vinylpyridine, 1-vinyl-2-pyrrolidinone, 1-vinyl-1,2,4-triazole,1-vinylimidazole, N-vinylcaprolactone, 4-acryloylmorpholine,5-vinyluracil, 4-acryloylmorpholine, N,N-dimethylacrylamide,2-vinyl-1,3-dioxolane, acrolein diethyl acetal, acrolein dimethylacetal, 4-vinyl-1,3-dioxolane-2-one, vinylbenzoic acid, 1-vinylbenzylalcohol, vinyl trifluoroacetate, 1-vinyl cyclohexanole, vinyloxytrimethylsilane, vinyltrimethylsilane, allyl trimethylsilane,triphenyl(vinyl)silane, and 2-isopropenyl-2-oxazoline.
 18. A method forimproving one or more of solubility and dispersancy of polar additivesor sludge in a lubricating oil by using as the lubricating oil aformulated oil comprising a lubricating oil basestock as a majorcomponent, and a lubricating oil cobasestock as a minor component;wherein said lubricating oil cobasestock comprises one or more compoundsrepresented by the formula:R₁—Si(R₃)₂—O—Si(R₄)₂—R₂  (1) wherein R₁ and R₂ are the same or differentand are the saturated residue of an olefin having from about 4 to about40 carbon atoms; and each R₃ and R₄ are the same or different and are analkyl group having from 1 to about 20 carbon atoms; wherein the olefinis selected from the group consisting of an aromatic olefin, acycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, avinyl ester, and a heteroatom-containing olefin; and wherein thelubricating oil cobasestock has a viscosity (Kv₁₀₀) from about 2 toabout 300 cst at 100° C., and a viscosity index (VI) from about −100 toabout 300.